ORIGINAL_ARTICLE
Melamine trisulfonic acid as a highly efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
Melamine trisulfonic acid (MTSA) is utilized as a highly efficient catalyst for the solvent-free condensation reaction of 2-naphthol (2 eq.) with arylaldehydes (1 eq.) under conventional thermal as well as microwave conditions to give the d
https://icc.journals.pnu.ac.ir/article_488_f3833fe36a88efe12dbf0239d50db239.pdf
2014-01-01
1
17
14-Aryl-14H-dibenzo[a
j]xanthene
melamine trisulfonic acid (MTSA)
2-naphtol
arylaldehyde
solvent-free
microwave
Abdolkarim
Zare
abdolkarimzare@yahoo.com
1
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
LEAD_AUTHOR
Fatemeh
Monfared
f.monfared66@gmail.com
2
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
AUTHOR
[1] T. Hideo, Chem. Abstr., 1981, 95, 80922b, Jpn. TokkyoKoho JP 56005480, 1981.
1
[2] R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parker, G.J. Thomas, PCT Int. Appl. WO9706178, 1997.
2
[3] J.P. Poupelin, G.S. Ruf, O.F. Blanpin, G. Narcisse, G.U. Ernouf, R. Lacroix, Eur. J. Med. Chem., 1978, 13, 67-71.
3
[4] R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochem. Pol., 1998, 45, 833-845.
4
[5] S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, D. Sun, B.B. Rosenblum, S.H. Khan, M. Taing, U.S. Patent 6, 2003, 583, 168.
5
[6] A. Bekaert, J. Andrieux, M. Plat, Tetrahedron Lett., 1992, 33, 2805-2806.
6
[7] S. Chatterjee, M. Iqbal, J.C. Kauer, J.P. Mallamo, S. Senadhi, S. Mallya, D. Bozyczko-Coyne, R. Siman, Bioorg. Med. Chem. Lett., 1996, 6, 1619-1622.
7
[8] A. Naya, M. Ishikawa, K. Matsuda, K. Ohwaki, T. Saeki, K. Noguchi, N. Ohtake, Bioorg. Med. Chem., 2003, 11, 875-884.
8
[9] I.Mohammadpoor-Baltork, M. Moghadam, V. Mirkhani, S. Tangestaninejad, H.R. Tavakoli, Chin. Chem. Lett., 2011, 22, 9-12.
9
[10] G. Karthikeyan, A. Pandurangan, J. Mol. Catal. A: Chem., 2009, 311,36-45.
10
[11] P.S. Kumar, B.S. Kumar, B. Rajitha, P.N. Reddy, N. Sreenivasulu, Y.T. Reddy, ARKIVOC,2006, xii, 46-50.
11
[12] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, E. Arzroomchilar, Bioorg. Med. Chem.Lett., 2008, 18, 436-438.
12
[13] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc.,2011, 8, 129-134.
13
[14] M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun.,2007, 8, 1595-1598.
14
[15] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Argoon, R. Roohandeh, J. Mol. Liq.,2012, 167, 69-77.
15
[16] M. Hong, C. Cai, J. Fluorine Chem.,2009, 130, 989-992.
16
[17] A.K. Bhattacharya, K.C. Rana, M. Mujahid, I. Sehar, A.K. Saxena, Bioorg. Med. Chem. Lett.,2009, 19, 5590-5593.
17
[18] G.I. Shakibaei, P. Mirzaei, A. Bazgir, Appl. Catal. A: Gen.,2007, 325, 188-192.
18
[19] W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Lett.,2008, 49, 3391-3394.
19
[20] A.R. Momeni, M. Sadeghi, Appl. Catal. A: Gen.,2009, 357, 100-105.
20
[21] A. Khalafi-Nezhad, A. Parhami, R. Bargebid, S. Molazade, A. Zare, H. Foroughi, Mol. Divers.,2011, 15, 373-381.
21
[22] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen.,2013, 467, 61-68.
22
[23] A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq., 2013, 186, 63-69.
23
[24] A.R. Kiasat, M. Fallah-Mehrjardi, Synth. Commun., 2010, 40, 1551-1558.
24
[25] F. Shirini, M.A. Zolfigol, J. Albadi, J. Iran. Chem. Soc., 2010, 7,895-899.
25
[26] F. Shirini, M.A. Zolfigol, J. Albadi, Chin. Chem. Lett., 2011, 22, 318-321.
26
[27] F. Shirini, M.A. Zolfigol, A.-R. Aliakbar, J. Albadi, Synth. Commun., 2010, 40, 1022-1028.
27
[28] F. Shirini, J. Albadi, Bull. Korean Chem. Soc.,2010, 31,1119-1120.
28
[29] K. Tanaka, Solvent-free Organic Synthesis, Wiley- VCH, GmbH and KGaA, Weinheim, 2004.
29
[30] A. Khazaei, M. A. Zolfigol, A.R. Moosavi-Zare, A. Zare, M. Khojasteh, Z. Asgari, V. Khakyzadeh, A. Khalafi- Nezhad, Catal. Commun.,2012, 20, 54-57.
30
[31] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A: Gen.,2011, 400, 70-81.
31
[32] A. Loupy, Microwave in Organic Synthesis, Wiley- VCH, Weinheim, 2006.
32
[33] A. Zare, A. Hasaninejad, A. Salimi Beni, A.R. Moosavi-Zare, M. Merajoddin, E. Kamali, M. Akbari-Seddigh, Z. Parsaee, Sci. Iran. C, 2011, 18, 433-438.
33
[34] B. Rajitha, B.S. Kumar, Y.T. Reddy, P.N. Reddy, N. Sreenivasulu, Tetrahedron Lett., 2005, 46, 8691-8693.
34
[35] T.S. Jin, J.S. Zhang, J.C. Xiao, A.Q. Wang, T.S. Li, Synlett, 2004, 866-870.
35
[36] A. Zare, M. Merajoddin, F. Abi, A.R. Moosavi-Zare, M. Mokhlesi, M.A. Zolfigol, Z. Asgari, V. Khakyzadeh, A. Hasaninejad, A. Khalafi-Nezhad, A. Parhami, J. Chin. Chem., Soc.,2012, 59, 860-865.
36
[37] M.A. Zolfigol, A.R. Moosavi-Zare, P. Arghavani-Hadi, A. Zare, V. Khakyzadeh, G. Darvishi, RSC Adv., 2012, 2, 3618-3620.
37
ORIGINAL_ARTICLE
Synthesis and characterization of derived imines from 4-imino-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-3(4H)-amine
The synthesis and characterization of derived imines from 4-imino-5,6,7,8-tetrahydro-1-benzo thieno[2,3-d]pyrimidin-3(4H)-amine 3 has been developed in 3 steps through the reaction of heteroaromatic o-aminonitrile 1 with triethyl orthoformate afforded the corresponding imido ester 2 followed by cyclization with hydrazine hydrate to furnish iminothienopyrimidineamine 3 and finally the imination of 3 at room temperature with aromatic aldehydes was generated the corresponding imines (5a-5h). The new products were obtained in high yield with an easy work-up in simple reaction along with the purification of products by non-chromatographic method. This general synthetic procedure can be extended to the preparation of wide variety of imines using o-aminonitrile bifunctional derivatives which synthesized by Gewald reaction.
https://icc.journals.pnu.ac.ir/article_492_186c53cdd736436899a4c3b08cddee08.pdf
2014-01-01
18
26
N-(Arylmethylene)-4-imino-5
6
7
8-tetrahydro-1-benzothieno[2
3-d]pyrimidin-3(4H)-amines
Mehdi
Soleimany
mehdi_soleimany2005@yahoo.com
1
Nothing
LEAD_AUTHOR
Jalil
Lari
j.lary2010@gmail.com
2
Associate Professor
AUTHOR
Hooshang
Vahedi
hooshangvahedi@yahoo.co.uk
3
Assistant Professor
AUTHOR
[1] F.Ahmeda,M.H.Hanna,M.F.Eman,E.AbdEl-Galil,World.J. Chem., 2009, 4, 58-65.
1
[2] N.Lakshmi,V.Haritha,V.Sreeram,D.Ra-jalakshmi,Rasayan. J. Chem., 2009, 2, 71-74.
2
[3] M.D.Salahuddin,K.Sunil,S.M.Shantakumar,E-Journal of Chemistry, 2009, 6, 801-808.
3
[4] L.P.Melissa,C.G.Wayne,E.J.Tara,A.N.Ja-son,Bioorg. Med. Chem.Lett., 2003, 13, 107-110.
4
[5] V. Alagarsamy, S.Vijayakumar,S.V. Raja, Biomed. Pharma., 2007,61, 285-291.
5
[6] A.V. Bol´but, M.V. Vovk, Abstracts of Interna- tional Confeerence on the Chemistry of Nitrogen Containing Heterocycles, CNH-2003, Kharkiv (Ukraine), 2003, p. 68.
6
[7] C.J. Shishoo, V.S. Shirsath, I.S. Rathod, V.D. Yande, Eur. J. Med. Chem., 2000, 35, 351-358.
7
[8] S.Sasaki,N.Cho, Y.Nara,M.Harada,S.Endo, N.Suzuki, Sh.Furuya,M. Fujino, J. Med. Chem., 2003, 46, 113-124.
8
[9] B.V. Ashalatha, B. Narayana, R.K. Vijaya, K.N. Suchetha, Eur. J. Med. Chem., 2007, 42, 719-728.
9
[10] V.Alagarsamy,D.Shankar,V.R.Solomon, Arkivoc, 2006, 11, 149-159.
10
[11] I.O.Donkor, H. Li, S.F. Queener,Eur. J. Med. Chem., 2003, 38, 605-611.
11
[12] C.J.Shishoo,M.B.Devani,U.S.Pathak,S. Ananthan, V.S.Bhadti,G.V. Ullas,K.S.Jain,I.S. Rathod,D.S.Talati,N.H. Doshi,J. Heterocycl. Chem., 1984, 21, 375-380.
12
[13] Z.Csuros, R.Soos,J. Palinkas,I.Bitter,Acta. Chim., 1971, 68, 397-402.
13
[14] F.Sauter,Monatsh.Chem.,1970,101,535-543.
14
[15] H. Link,Helv. Chim. Acta., 1990, 73, 797-803.
15
[16] A. Davoodnia, M.Bakavoli,M.Soleimany,N. Tavakoli-Hoseini,Monatsh.Chem.,2009,140,355-358.
16
[17] K.Gewald,E.Schinke,H.Boettcher,Chem. Ber., 1966, 99, 94-100.
17
ORIGINAL_ARTICLE
Catalytic application of an organosuperbase denderon grafted on mesoporous SBA-15 and related palladium complex in the aerobic oxidation of alcohols
An efficient synthetic method for successful synthesis of amine denderon on SBA-15 and related Pd (II) complex has been developed. This modified mesoporous material was characterized by various techniques such as TEM, XRD, atomic absorption spectroscopy, N2 adsorption-desorption, and FT-IR. The catalytic activities of the prepared catalysts were investigated by employing aerobic oxidation of alcohols as model reactions. The yields of the products were in the range from 75% to 92%. The catalyst can be readily recovered and reused at least 5 consecutive cycles without significant leaching and loss its catalytic activity. Organosuperbase, SBA-15, Palladium complex, Oxidation Organosuperbase, SBA-15, Palladium complex, Oxidation
https://icc.journals.pnu.ac.ir/article_606_232ead21dad73fccd43474dbe055ffc0.pdf
2014-01-01
27
33
Organosuperbase
SBA-15
palladium complex
Oxidation
Hojat
Veisi
hojatveisi@yahoo.com
1
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
LEAD_AUTHOR
Davood
Kordestani
davood_k82@yahoo.com
2
Medical biology Research Center, Kermanshah University of Medical Sciences, Kermanshah-Iran
AUTHOR
Sami
Sajjadifar
ss_sajjadifar@yahoo.com
3
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
AUTHOR
Mona
Hamelian
h_organo2007@yahoo.com
4
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
AUTHOR
[1]. A. Anan, K.K. Sharma, T. Asefa, J. Mol. Catal. A: Chem.,2008, 288, 1-13.
1
[2] Z. Zhou, Q. Meng, A. Seifert, A. Wagener, Y. Sun, S. Ernst, W.R. Thiel, Micropo. Mesopor. Mat., 2009, 121, 145-151.
2
[3] Q. Meng, X. Zhang, C. He, P. Zhou, W. Su, C. Duan, Talanta , 2011, 84, 53-59.
3
[4] S. Somacescu, P. Osiceanu, J.M. Calderon Moreno, L. Navarrete, J.M. Serra, Micropor. Mesopo. Mat.,2013, 179, 78-88.
4
[5] S. Tao, Z. Zhu, C. Meng, C. Wang, Micropor. Mesopor. Mat., 2013, 171, 94-102.
5
[6] M. Mazloum-Ardakani, M.A. Sheikh-Mohseni, M. Abdollahi-Alibeik, A. Benvidi, Sensor. Act.B: Chem., 2012, 171–172, 380-386.
6
[7] K. Dhahagani, J. Rajesh, R. Kannan, G. Rajagopal, Tetrahedron: Asymmetry,2011, 22, 857-865.
7
[8] M. Ghashghaee, R. Karimzadeh, Micropor. Mesopor. Mat., 2013, 170, 318-330.
8
[9] S.L. Hruby, B.H. Shanks, J. Catal., 2009, 263, 181-188.
9
[10] M.N. Parvin, H. Jin, M.B. Ansari, S.-M. Oh, S.-E. Park, Appl. Catal. A: Gen., 2012, 413-414,205-212.
10
[11] Q. Wang, V.V. Guerrero, A. Ghosh, S. Yeu, J.D. Lunn, D.F. Shantz, J. Catal., 2010, 269, 15-25.
11
[12] T. Yokoi, Y. Kubota, T. Tatsumi, Appl. Catal. A: Gen., 2012, 421–422, 14-37.
12
[13] Y. Shao, J. Guan, S. Wu, H. Liu, B. Liu, Q. Kan, Micropor. Mesopor. Mat., 2010, 128,120-125.
13
[14] J. Demel, J. Čejka, P. Štěpnička, J. Mol. Catal. A: Chem.,2010, 329, 13-20.
14
[15] M.-J. Jin, A. Taher, H.-J. Kang, M. Choi, R. Ryoo, Green Chem., 2009, 11, 309-313.
15
[16] W. Chen, P. Li, L. Wang, Tetrahedron,2011, 67, 318-325.
16
[17] J.C. Hicks, R. Dabestani, A.C. Buchanan, C.W. Jones, Chem. Mat., 2006, 18, 5022-5032.
17
[18] H. Li, J. Lü, Z. Zheng, R. Cao, J. Colloid Inter. Sci., 2011, 353, 149-155.
18
[19] M. Bhagiyalakshmi, S.D. Park, W.S. Cha, H.T. Jang, Appl. Sur. Sci., 2010, 256, 6660-6666.
19
[20] A. Shahbazi, H. Younesi, A. Badiei, Chem. Eng. J., 2011, 168, 505-518.
20
[21] A. Alizadeh, M.M. Khodaei, D. Kordestani, A.H. Fallah, M. Beygzadeh, Micropor. Mesopor. Mat., 2012, 159, 9-16.
21
[22] A. Alizadeh, M.M. Khodaei, D. Kordestania, M. Beygzadeh, J. Mol. Catal. A: Chem., 2013, 372, 167-174.
22
[23] H. Veisi, D. Kordestani, A.R. Faraji J. Porous Mater., 2013, doi:10.1007/s10934-013-9758-3.
23
ORIGINAL_ARTICLE
Isolation, identification and characterization of lawsone from henna leaves powder with soxhlet technique
Lawsone a natural pigment present in the henna leaves has been used as a skin and hair dye since 1400 BC. The concentration of this natural compound in leaves varies from place to place depending upon many of the environmental factors and the highest quantity reported so far is about 1% of the dry mass. Heretofore, it has been reported that natural colored extracts and isolate from Henna leaves with many methods such as maceration, digestion, microwave and infusion. In this paper, regarding the therapeutic effects and traditional applications of henna, it was tried to isolate and characterize Lawsone from the henna leaves marketed in Tabriz city of Iran by soxhlet extraction technique in methanol solvent. The advantage of this technique is the isolation of large amounts of lawsone (720 mg from 40 g henne leaves powder) with smaller quantity of methanol.
https://icc.journals.pnu.ac.ir/article_675_6773170b4fb967bad8b5e7ca9e0cc69f.pdf
2014-01-01
34
38
henna
Lawsonia inermis L
lawsone
isolation
soxhlet extractor
Mehrdad
Mahkam
mehdi_1046@yahoo.com
1
Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran
AUTHOR
Mehdi
Nabati
mnabati@ymail.com
2
Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran
LEAD_AUTHOR
Hadieh
Rahbar Kafshboran
hadiehrahbar@gmail.com
3
Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz, Iran
AUTHOR
[1] S.C. Chen, C.H. Chen, C.L. Chern, L.S. Hsu, Y.C. Huang, K.T. Chung, S.M. Chye, Toxicol. in Vitro. 2006, 20, 801-807.
1
[2] Y.C. Huang, W.C. Hung, W.Y. Kang, W.T. Chen, C.Y. Chai, Toxicol. Lett.2007, 170, 116-123.
2
[3]A. Tamkoc, E. Arsalan, Pak. J. Bot. 2011, 43, 1105-1110.
3
[4] M. Mahkam, M. Nabati, A. Latifpour, J. Aboudi, Des. Monomers Polym.2014, 17, 453-457.
4
[5] B.S. Nayak, G. Isitor, E.M. Davis, G.K. Pillai, Phytotherapy Research. 2007, 21, 827-831.
5
[6] J.M. White, P. Kullavanijaya, I. Duangdeeden, R. Zazzeroni, N.J. Gilmour, D.A. Basketter, J.P. Mc Fadden, Clin. Exp. Allergy.2006, 36, 1289-1293.
6
[7]M. Shahid Khan, Z.H. Khan, Spectrochimica Acta Part A. 2005, 61,777-790.
7
[8]T. Satoh, T. Tsuji, H. Matsuda, S. Sudoh, Bull. Chem. Soc. Jpn. 2007, 80, 321-323.
8
[9]M. Nabati, M. Mahkam, Iran. Chem. Commun.,2014, 2, 129-136.
9
[10] E.W.C. Chan, Y.Y. Lim, S.K. Wong, S.P. Tan, F.S.Lianto, M.Y. Yong, Food Chemistry.2009, 113, 166–172.
10
[11] M. Zada, Z.K. Shinwari, N. Zakir, M.A. Rabbani, Pak. J. Bot.,2013, 45,443-448.
11
[12]H. Ohtsu, Z.Y. Xiao, J. Ishida, M. Nagai, H.K. Wang, H. Itokawa, C.Y. Su, C. Shih, T.Y. Chiang, E. Chang, Y.F. Lee, M.Y. Tsai, C.S. Chang, K.H.J. Lee, Med. Chem. 2002, 45, 5037-5042.
12
[13]A. Tamkoc, E. Arsalan, Pak. J. Bot., 2011, 43, 1105-1110.
13
ORIGINAL_ARTICLE
Potassium carbonate: a highly efficient catalyst for the acylation of alcohols, phenols and thiols under mild conditions
A general, mild and efficient protocol has been developed for the synthesis of esters and thioesters. The process has been taking place using tetra n-butylammonium iodide (TBAI) as a phase-transfer catalyst and in the presence of potassium carbonate (K2CO3). A wide range of esters and thioesters was prepared in high yields and suitable times by the treatment of alcohols, phenols and thiols with acetic anhydride. Acylation reactions of a number of alcohols, phenols and thiols with acetic anhydride demonstrated that Potassium carbonate is a convenient and efficient catalyst for the synthesis of esters and thioesters. This is a mild, general and practical procedure for the synthesis of esters and thioesters in high yields and suitable times.
https://icc.journals.pnu.ac.ir/article_542_088325fa856bf1ad1710d93c6864e879.pdf
2014-01-01
39
47
acylation
esters
thioesters
tetra n-butylammonium iodide
potassium carbonate
acetic anhydride
Mostafa
Kazemi
mostaffa_kazemi@yahoo.com
1
methodology
LEAD_AUTHOR
Homa
Kohzadi
kohzadi_1389@yahoo.com
2
chemistry
AUTHOR
Zahra
Noori
noori.zahra1368@gmail.com
3
chemistry
AUTHOR
[1] J. Ko, J. Ham, I.Yang, J. Chin, S.J. Nam, H. Kang, Tetrahedron Lett., 2006, 47, 7101–7106.
1
[2] J.L.Yu, H. Wang, K.F. Zou, J.R .Zhang, X. Gao, D.W. Z.T. Li. Zhang, Tetrahedron, 2013, 69,310–315.
2
[3] A. Vakalopoulos, X. Kavazoudi, J. Schoof, Tetrahedron Lett., 2006,47, 8607–8610.
3
[4] A.B. Naidu, G. Sekar, Tetrahedron Lett., 2008, 49, 3147–3151.
4
[5] A. Kamal, M. N. A. Khan, K. S. Reddy, Y.V.V. Srikanth, T. Krishnaji, Tetrahedron,2007,48, 3813–3818.
5
[6] C. Peppe, L.B.D. Castro, J. Can, Chem., 2009, 87, 678-683.
6
[7] M.M. Lakouraj, B. Movassagh, Z. Fadaei, Monat. Chem., 2002, 133, 1085-1088.
7
[8] D.S. Kanta, Tetrahedron Lett., 2004, 45, 2919–2922.
8
[9] A. Orita, C. Tanahashi, A. Kakuda , J OteraAngewChemInt Ed., 2000, 39, 2877-2879.
9
[10] S.V. Pansare, M.G. Malusara, A.N. Rai, Synth Commun ., 2000, 30, 2587-2592.
10
[11] B.C. Ranu, P. Dutta, A. Sarkar, J Chem Soc Perkin Trans., 2000, 1, 2223-2225.
11
[12] S.T.A. Shah, K.M. Khan, H. Hussain, M.U. Anwar, M. Fecker,Tetrahedron,2005, 61, 6652-6656.
12
[13] S.T.A. Shah, K.M. Khan, A.M. Heinrich, W. Voelter, Tetrahedron Lett., 2002, 43, 8281-8283.
13
[14] S.G. Lee, J.H. Park, J MolCatal A. Chem., 2003,194, 49-52.
14
[15] M. Kazemi, Z. Noori, H. Kohzadi, M. Sayadi, A. Kazemi, Iranian Chemical Communication, 2013, 1, 20-25.
15
[16] S.T. Kadam, H. Lee, S.S. Kim, Bull. Korean Chem. Soc.,2009,30, 1071–1076.
16
[17] P.R. Gustavo, O. Danirel, C. Bennardi, A. Juan, T.B. Auyinograciel, J.T. Horacio, E-journal of chemistery., 2008, 5, 541-547.
17
[18] G. Rina, Tetrahedron, 2005, 46, 147–151.
18
ORIGINAL_ARTICLE
A practical and convenient method for the synthesis of anesthetic drug thiopental: using thiourea and sodium ethoxide
A general, simple, practical and convenient method has been described for the synthesis of anesthetic drug thiopental using thiourea in the presence of sodium ethoxide. Anesthetic drug of thiopental was prepared in two stages; during the first stage, the alkylation of mthyl cyanoacetate was performed which was then to be followed by cyclization. Alkylation of methyl cyanoacetate which was performed by 2-iodopentane in the presence of sodium ethoxide reacts with thiourea and then the process was followed by thiopental prepration in excellent yield. Some important aspects of this methodology are the high reactivity of the substrates, avoidance of the use of hazardous solvents, simplicity of the product separation, low cost of the substrates and reagents and high yield of product. This is a applicable and efficient method for the preparation of thiopental anesthesia in high yield and in an appropriate time.
https://icc.journals.pnu.ac.ir/article_543_3a825ec06b6f8b60be3a9450b03ab821.pdf
2014-01-01
48
55
Thiopental
drug
anesthetic
mthyl cyanoacetate
thiourea
Synthesis
Hojat
Narimani
h.narimani64@yahoo.com
1
chemistry
LEAD_AUTHOR
Mostafa
kazemi
mostaffa_kazemi@yahoo.com
2
methodology
AUTHOR
Homa
Kohzadi
kohzadi_1389@yahoo.com
3
chemistry
AUTHOR
[1] E.R. Garrett, J.T. Bojarski, G.J. Yakatan, Journal of Pharmaceutical Science,1971, 60, 1145-1154.
1
[2] C.H. Suk Kyu, D.H. Andrew, J. Am. Chem. Soc., 1988, 110, 1318–1319.
2
[3] D. Thetford, A.P. Chorlton, J. Hardman, Dyes and Pigments, 2003, 59, 185-195.
3
[4] N. Harrison, W. Mendelson, H.D. Wit, Neuropsychopharmacology, 2000, 15, 172-176.
4
[5] H. Russo, J. Brès, M.P. Duboin, B. Roquefeuil., Eur. J. Clin. Pharmacol., 1995, 49, 127–137.
5
[6] D.J. Morgan, G.L. Blackman, J.D. Paull, L.J. Wolf, Anesthesiology, 1981, 54, 474–480.
6
[7] M.M. Margaret, C. Beyer, B.R. Komisaruk, Pharmacology Biochemistry and Behavior, 1989, 32, 897-900.
7
[8] A. Kushikata, T. Hirota, K. Yoshida, H. Kudo, M. Lambert, D.G. Smart, D. Jerman, J.C. Matsuki, Neuroscience., 2003, 121, 855-863.
8
[9] H. Downes, D.R. Koop, B. Klopfenstein, N. Lessov, Comparative Biochemistry and Physiology, 1999,124, 203-210.
9
[10] H.K. Zak, FEBS Letters, 1976, 63, 149-153.
10
[11] K.h. Mohammed Khan, A. Wadood, Z. Ulhaq, M. Khan, M. Arif Lodhi, H. Perveen, M. Iqbal Choudhary, W. Voelter, Journal of Molecular Graphics and Modelling., 2011,30, 153-156
11
[12] Dhirendra Mehta, Edwin L. Bradley Jr., Igor Kissin., Journal of Clinical Anesthesia, 1991,3, 280-284.
12
[13] J.C. Mucklow, Side Effects of Drugs Annual, 1989,13, 50-55.
13
[14] S. Ahadi, M. Abaszadeh, H.R. Khavasi, A. Bazgir, Tetrahedron,2012, 68, 2906-2916.
14
[15] J. Daniel Figueroa-Villar, A.A. Vieira, Journal of Molecular Structure,2013, 1034, 310-317.
15
[16] M.d. Amin Hasan, A. Seshaditya, S. Zalis, L. Mishra, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.,2011, 83, 532-539.
16
[17] A.J. Davies, xPharm. The Comprehensive Pharmacology Reference, 2007, 1-4.
17
[18] M.J. McLeish., Analytical Profiles of Drug Substances and Excipients, 1992,21, 535-572.
18
[19] V.M. Okudzhara,, A. Izv, N. Gruz, Ser. Biol. 1988,14, 58-66.
19
[20] L.V. Jones, M.J. Whilehouse, Biomed. Mass Spectrum, 1981,8,226-231.
20
[21] V.I. Popora, V.F. Kramarenko, Farmatsia (Moscow),1974,23, 148-157.
21
ORIGINAL_ARTICLE
An improved structure models to explain retention behavior of atmospheric nanoparticles
The quantitative structure-retention relationship (QSRR) of nanoparticles in roadside atmosphere against the comprehensive two-dimensional gas chromatography which was coupled to high-resolution time-of-flight mass spectrometry was studied. The genetic algorithm (GA) was employed to select the variables that resulted in the best-fitted models. After the variables were selected, the linear multivariate regressions [e.g. the partial least squares (PLS)] as well as the nonlinear regressions [e.g. the kernel PLS (KPLS) and Levenberg- Marquardt artificial neural network (L-M ANN)] were utilized to construct the linear and nonlinear QSRR models. The correlation coefficient cross validation (Q2) and relative error for test set L-M ANN model are 0.939 and 4.89, respectively. The resulting data indicated that L-M ANN could be used as a powerful modeling tool for the QSPR studies.
https://icc.journals.pnu.ac.ir/article_595_f910d1f7f33307691bcc05e273d00314.pdf
2014-01-01
56
71
Atmospheric nanoparticles
QSRR
GA-KPLS
Levenberg -Marquardt artificial neural network
Sharmin
Esmaeilpoor
esmaeilpoor@yahoo.com
1
Department of Chemistry, Payame Noor University of ilam, Ilam, Iran
AUTHOR
Zahra
Shirzadi
zahrashirzadi@yahoo.com
2
Department of chemistry, Islamic Azad University, Shahreza Branch, Isfahan, Iran
AUTHOR
Hadi
noorizadeh
hadinoorizadeh@yahoo.com
3
Department of Chemistry, Payame Noor University of ilam, Ilam, Iran
LEAD_AUTHOR
[1] D.M. Brown, M.R.Wilson, W. MacNee, V. Stone, K. Donaldson, Toxicol. Appl. Pharm., 2001, 175, 191-199.
1
[2] K. Inoue, H. Takano, R. Yanagisawa, M. Sakurai, T. Ichinose, K. Sadakane, T. Yoshikawa, Respir. Res., 2005, 6, 106-113.
2
[3] G. Buzorius, A. Zelenyuk, F. Brechtel, D. Imre, Geophys Res Let., 2002, 29, 1974–1978.
3
[4] Zh. Chong-Shu, Ch-Ch. Chen, J-J. Cao, Ch-J. Tsai, Ch.C.-K. Chou, Sh-Ch. Liu, Atmos. Environ, 2010, 44, 2668-2673.
4
[5] S.S. Hang Ho, J. Zh. Yu, J. Chromatogr. A, 2004, 1059, 121–129.
5
[6] J. Dallüge, M. van Rijn, J. Beens, R.J.J. Vreuls, U.A.Th.Brinkman, J. Chromatogr. A, 2002, 965, 207-217.
6
[7] F. Adam, F. Bertoncini, N. Brodusch, E. Durand, D. Thiebaut, D. Espinat, M-C. Hennion, J. Chromatogr. A, 2007, 1148, 55–64.
7
[8] T. Hyölyläinen, M. Kallio, M. Shimmo, K. Saamio, K. Hartonen, M.L. Riekkola, in: Presentation at the First International Symposium on Two-Dimensional Gas Chromatography, Volendam, The Netherlands, 2003.
8
[9] C. Muhlen, C. Alcaraz Zini, E.B. Caramao, P.J. Marriott, J. Chromatogr. A., 2008, 1200, 34–42.
9
[10] M. Adahchour, M. Brandt, H.U. Baier, R.J.J. Vreuls, A.M. Batenburg, U.A.Th. Brinkman, J. Chromatogr. A., 2004, 1054, 57-65.
10
[11] J.F. Hamilton, P.J. Webb, A.C. Lewis, J.R. Hopkins, S. Smith, P. Davy, Atmos. Chem. Phys., 2004,4, 1279-1290.
11
[12] N. Ochiai, T. Ieda, K. Sasamoto, A. Fushimi, Sh. Hasegawa, K. Tanabe, Sh. Kobayashi, J. Chromatogr. A., 2007, 1150, 13–20.
12
[13] J. Leban, M. Baierl, J. Mies, V. Trentinaglia, S. Rath, K. Kronthaler, K. Wolf, A. Gotschlich, M.H.J. Seifert, J. Bioorg. Med. Chem. Lett.,2007, 17, 5858–5862.
13
[14] K. Bodzioch, A. Durand, R. Kaliszan, T. Bączek, Y. Vander Heyden, Talanta, 2010, 81, 1711-1718
14
[15] S. Riahi, E. Pourbasheer, M.R. Ganjali, P. Norouzi, J.Hazard.Mater.,2009, 166, 853-859.
15
[16] S.H. Woo, J. ChO, Y.S. Yun, H. Choi, Ch.S. Lee, D.S. Lee, J. Hazard. Mater.,2009, 161, 538–544
16
[17] N. Krämer, A.L. Boulesteix, G. Tutz, Chemom. Intell. Lab. Syst., 2008, 94, 60–69.
17
[18] S. Haykin, Neural Networks, Prentice-Hall, New Jersey, 1999.
18
[19] R. Todeschini, V.Consonni, A.Mauri, M.Pavan, DRAGON-Software for the calculation of molecular descriptors. Version 3.0 for Windows, 2003.
19
[20] D.E. Goldberg, Genetic Algorithms in Search, Optimization and Machine Learning, Addison-Wesley–Longman, Reading, MA, USA, 2000.
20
[21] S. Riahi, E. Pourbasheer, R. Dinarvand, M.R. Ganjali, P. Norouzi, Exploring QSARs for antiviral activity of 4-alkylamino-6-(2-hydroxyethyl)-2- methylthiopyrimidines by support vector machine, Chem. Biol. Drug Des, 2008, 72, 205-216.
21
[22] J.A.d. Sousa, M.C. Hemmer, J. Casteiger, Prediction of H-1 NMR chemical shifts using neural networks, Anal. Chem., 2002, 74, 80-93.
22
[23] U. Depczynski, V.J. Frost, K. Molt, Genetic algorithms applied to the selection of factors in principal component regression, Anal. Chim. Acta., 2000, 420, 217-227.
23
[24] S. Wold, M. Sjostrom, L. Eriksson, PLS-regression: a basic tool of chemometrics, Chemom. Intell. Lab. Syst., 2001, 58, 109-130.
24
[25] B.M. Nicolai, K.I. Theron, J. Lammertyn, Chemom. Intell. Lab. Syst.,2007, 85, 243–252
25
[26] R. Rosipal, L.J. Trejo, J. Mach. Learning Res.,2001, 2, 97-123.
26
[27] J. Zupan, J. Gasteiger, Neural Network in Chemistry and Drug Design, Wiley–VCH, Weinheim, 1999.
27
[28] S. Kara, A.S. Güven, M. Okandan, F. Dirgenali, Comput. Biol. Med., 2006, 36, 473–483
28
[29] A. Yasri, D. Hartsough, J. Chem. Inf. Comput. Sci., 2001, 41, 1218-1227
29
[30] S. Kara, M. Okandan, Pattern Recognit,2007,40, 2967 – 2973
30
[31] M. Salvi, D. Dazzi, I. Pelistri, F. Neri, J.R. Wall, Ophthalmology, 2002, 109, 1703-1708.
31
[32] K.Kim, J.M.Lee, I.B. Lee, Chemom. Intell. Lab. Syst., 2005, 79, 22-30.
32
[33] J. Acevedo-Martınez, J.C. Escalona-Arranz, A. Villar-Rojas, F. Tellez-Palmero, R. Perez-Roses, L. Gonzalez, R. Carrasco-Velar, J. Chromatogr. A., 2006, 1102, 238-244.
33
[34] A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, Bioorg. Med. Chem., 2006, 14, 6686-6694.
34
[35] A. Golbraikh, A. Tropsha, J. Mol. Graphics Modell, 2002, 20, 269-276.
35
[36] R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, Germany, 2000.
36
ORIGINAL_ARTICLE
Dipyridine cobalt chloride as an efficient and chemoselective catalyst for the synthesis of 1,1-diacetates under solvent-free conditions
1,1-Diacetates(acylals) were prepared by direct condensation of various aldehydes with acetic anhydride using dipyridine cobalt chloride (CoPy2Cl2) as an efficient and green catalyst under solvent-free conditions at room temperature. The important features of this catalyst method are that the catalyst is solid, stable at high temperatures, soluble in water, stable in air, immiscible in common organic solvents, low toxic and, above all, it is reusable. CoPy2Cl2 can be recycled after a simple work-up and reused at least five runs without appreciable loss of its catalytic activity. High chemo-selectivity toward aldehyde in the presence of ketones is another advantage of the present method which provides selective protection of aldehydes in their mixtures with ketones.
https://icc.journals.pnu.ac.ir/article_593_93d9aa62e6d3605e44ac3825d639af9f.pdf
2014-01-01
72
81
CoPy2Cl2
acylation
Protection
solvent-free conditions
carbonyl protection
Sobhan
Rezayati
sobhan.rezayati@yahoo.com
1
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
LEAD_AUTHOR
Zahra
Erfani
zahraerfani34@yahoo.com
2
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
AUTHOR
Saman
Rezayati
saman.rezayati@yahoo.com
3
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
AUTHOR
Rahimeh
Hajinasiri
rhmhajinasiri@yahoo.com
4
Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, I. R. Iran
AUTHOR
Marzieh
Rekavandi
marziehrekavandi@yahoo.com
5
Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, I. R. Iran
AUTHOR
[1] T.W. Greene, P.G.M. Wuts, Wiley: New York, 1991.
1
[2] M.J.J. Gregory, Chem. Soc., 1970, (B), 1201-1207.
2
[3] H.W. Pinnick, K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N.J. Radhakrishna, Org. Chem., 1983, 48, 1765-1767.
3
[4] H. Held, A. Rengstle, D. Mayer, Gerhartz, New York, 1985, A1, 68.
4
[5] J.G. Frick, R.J. Harper, J. Appl. Polym. Sci., 1984, 1433.
5
[6] W.R. Eanderson, Eur. Pat. Appl. EP 125, 781; Chem. Abstr., 1985, 103, P64010K.
6
[7] B. Karimi, J.J. Maleki, Org. Chem., 2003, 68, 4951-4954.
7
[8] J.S. Yadav, B.V.S. Reddy, Ch. Srinivas, Synth. Commun., 2002, 32, 2169-2174.
8
[9] M.J.J. Gregory, Chem. Soc. (B), 1970, 1201-1207.
9
[10] B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett., 2000, 5, 623-624.
10
[11] S.C. Roy, B. Banerjee, Synlett., 2002, 1677-1678.
11
[12] N. Deka, R. Borah, D.J. Kalita, J.C.J. Sarma, Chem. Res., 1998, (S), 94-95.
12
[13] N. Deka, D.J. Kalita, R. Borah, J.C.J. Sarma, Org. Chem., 1997, 62, 1563-1564.
13
[14]J.K. Michie, J.A. Miller, Synthesis, 1981, 824-824.
14
[15] S. Sajjadifar, S. Rezayati, Chemicalpapers, 2014, 68, 531-539.
15
[16] S. Sajjadifar, Omid Louie, J.Chem., 2013, 2013, 6 pages.
16
[17] S. Sajjadifar, International Journal of ChemTech Research., 2013, 5, 385-389.
17
[18] S. Sajjadifar, S. Rezayati, International Journal of ChemTech Research, 2013, 5, 1964-1968.
18
[19] J. VenuMadhav, B. Suresh Kuarm, B. Rajitha, ARKIVOC, 2008 (ii), 204-209.
19
[20] M.M. Heravi, K. Bakhtiari, S. Taheri, H.A. Oskooie, Green Chem., 2005, 7, 867–869.
20
[21] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, CatalCommun., 2008, 9, 89–96.
21
[22] A.T. Khan, L.H. Choudhury, S.J. Ghosh, MolCatal A Chem., 2006, 255, 230-235.
22
[23] A. Saini, S. Kumar, J.S. Sandhu, Synth Commun., 2007, 38, 106–113.
23
[24] A.R. Hajipour, A. Zarei, A.E. Ruoho, Tetrahedron Lett., 2007, 48, 2881-2884.
24
[25] R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, J. Mol. Catal A: Chem., 2004, 215, 49-53.
25
[26] N.M. Nagy, M.A. Jakab, J. Konya, and S. Antus, Appl. Clay. Sci., 2002, 21, 213-216.
26
[27] K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Raja-dhyaksha, H.W.J. Pinnick, Org. Chem.,1983, 48, 1765.
27
[28] H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Tetrahedron Lett., 2003, 44, 3951.
28
[29] A.T. Khan, L.H. Choudhury, S. Ghosh, Eur. J. Org. Chem., 2005, 13, 2782-2787.
29
[30] S.A. Pourmousavi, Z. Zinati, Turk J Chem., 2009, 33, 385-392.
30
[31] Q. Liu, H.M. Ai, S. Feng, Synth. Commun., 2012, 42, 122-127.
31
[32] B. RabindranJermy, A. Pandurangan, Catal. Commun., 2008, 9, 577-583.
32
[33] M. NouriSefat, A. Deris, K. Niknam, Chin. J. Chem., 2011, 29, 2361-2367.
33
[34] A.V. Reddy, K. Ravinder, V.L.N. Reddy, V. Ravinkanth, Y. Yenkateswarlu, Synth. Commun., 2003, 33, 1531-1536.
34
[35] A. Zare, A. Hasaninejad, E. Rostami, A.R. Moosavi-zare, M. Merajoddin, A. Arghoon, N. Pishahang, M. Shekouhy, E-Journal of Chemistry, 2009, 6, 390-396.
35
[36] A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun., 2008, 9, 89-96.
36
[1] D.M. Brown, M.R.Wilson, W. MacNee, V. Stone, K. Donaldson, Toxicol. Appl. Pharm., 2001, 175, 191-199.
37
[2] K. Inoue, H. Takano, R. Yanagisawa, M. Sakurai, T. Ichinose, K. Sadakane, T. Yoshikawa, Respir. Res., 2005, 6, 106-113.
38
[3] G. Buzorius, A. Zelenyuk, F. Brechtel, D. Imre, Geophys Res Let., 2002, 29, 1974–1978.
39
[4] Zh. Chong-Shu, Ch-Ch. Chen, J-J. Cao, Ch-J. Tsai, Ch.C.-K. Chou, Sh-Ch. Liu, Atmos. Environ, 2010, 44, 2668-2673.
40
[5] S.S. Hang Ho, J. Zh. Yu, J. Chromatogr. A, 2004, 1059, 121–129.
41
[6] J. Dallüge, M. van Rijn, J. Beens, R.J.J. Vreuls, U.A.Th.Brinkman, J. Chromatogr. A, 2002, 965, 207-217.
42
[7] F. Adam, F. Bertoncini, N. Brodusch, E. Durand, D. Thiebaut, D. Espinat, M-C. Hennion, J. Chromatogr. A, 2007, 1148, 55–64.
43
[8] T. Hyölyläinen, M. Kallio, M. Shimmo, K. Saamio, K. Hartonen, M.L. Riekkola, in: Presentation at the First International Symposium on Two-Dimensional Gas Chromatography, Volendam, The Netherlands, 2003.
44
[9] C. Muhlen, C. Alcaraz Zini, E.B. Caramao, P.J. Marriott, J. Chromatogr. A., 2008, 1200, 34–42.
45
[10] M. Adahchour, M. Brandt, H.U. Baier, R.J.J. Vreuls, A.M. Batenburg, U.A.Th. Brinkman, J. Chromatogr. A., 2004, 1054, 57-65.
46
[11] J.F. Hamilton, P.J. Webb, A.C. Lewis, J.R. Hopkins, S. Smith, P. Davy, Atmos. Chem. Phys., 2004,4, 1279-1290.
47
[12] N. Ochiai, T. Ieda, K. Sasamoto, A. Fushimi, Sh. Hasegawa, K. Tanabe, Sh. Kobayashi, J. Chromatogr. A., 2007, 1150, 13–20.
48
[13] J. Leban, M. Baierl, J. Mies, V. Trentinaglia, S. Rath, K. Kronthaler, K. Wolf, A. Gotschlich, M.H.J. Seifert, J. Bioorg. Med. Chem. Lett.,2007, 17, 5858–5862.
49
[14] K. Bodzioch, A. Durand, R. Kaliszan, T. Bączek, Y. Vander Heyden, Talanta, 2010, 81, 1711-1718
50
[15] S. Riahi, E. Pourbasheer, M.R. Ganjali, P. Norouzi, J.Hazard.Mater.,2009, 166, 853-859.
51
[16] S.H. Woo, J. ChO, Y.S. Yun, H. Choi, Ch.S. Lee, D.S. Lee, J. Hazard. Mater.,2009, 161, 538–544
52
[17] N. Krämer, A.L. Boulesteix, G. Tutz, Chemom. Intell. Lab. Syst., 2008, 94, 60–69.
53
[18] S. Haykin, Neural Networks, Prentice-Hall, New Jersey, 1999.
54
[19] R. Todeschini, V.Consonni, A.Mauri, M.Pavan, DRAGON-Software for the calculation of molecular descriptors. Version 3.0 for Windows, 2003.
55
[20] D.E. Goldberg, Genetic Algorithms in Search, Optimization and Machine Learning, Addison-Wesley–Longman, Reading, MA, USA, 2000.
56
[21] S. Riahi, E. Pourbasheer, R. Dinarvand, M.R. Ganjali, P. Norouzi, Exploring QSARs for antiviral activity of 4-alkylamino-6-(2-hydroxyethyl)-2- methylthiopyrimidines by support vector machine, Chem. Biol. Drug Des, 2008, 72, 205-216.
57
[22] J.A.d. Sousa, M.C. Hemmer, J. Casteiger, Prediction of H-1 NMR chemical shifts using neural networks, Anal. Chem., 2002, 74, 80-93.
58
[23] U. Depczynski, V.J. Frost, K. Molt, Genetic algorithms applied to the selection of factors in principal component regression, Anal. Chim. Acta., 2000, 420, 217-227.
59
[24] S. Wold, M. Sjostrom, L. Eriksson, PLS-regression: a basic tool of chemometrics, Chemom. Intell. Lab. Syst., 2001, 58, 109-130.
60
[25] B.M. Nicolai, K.I. Theron, J. Lammertyn, Chemom. Intell. Lab. Syst.,2007, 85, 243–252
61
[26] R. Rosipal, L.J. Trejo, J. Mach. Learning Res.,2001, 2, 97-123.
62
[27] J. Zupan, J. Gasteiger, Neural Network in Chemistry and Drug Design, Wiley–VCH, Weinheim, 1999.
63
[28] S. Kara, A.S. Güven, M. Okandan, F. Dirgenali, Comput. Biol. Med., 2006, 36, 473–483
64
[29] A. Yasri, D. Hartsough, J. Chem. Inf. Comput. Sci., 2001, 41, 1218-1227
65
[30] S. Kara, M. Okandan, Pattern Recognit,2007,40, 2967 – 2973
66
[31] M. Salvi, D. Dazzi, I. Pelistri, F. Neri, J.R. Wall, Ophthalmology, 2002, 109, 1703-1708.
67
[32] K.Kim, J.M.Lee, I.B. Lee, Chemom. Intell. Lab. Syst., 2005, 79, 22-30.
68
[33] J. Acevedo-Martınez, J.C. Escalona-Arranz, A. Villar-Rojas, F. Tellez-Palmero, R. Perez-Roses, L. Gonzalez, R. Carrasco-Velar, J. Chromatogr. A., 2006, 1102, 238-244.
69
[34] A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, Bioorg. Med. Chem., 2006, 14, 6686-6694.
70
[35] A. Golbraikh, A. Tropsha, J. Mol. Graphics Modell, 2002, 20, 269-276.
71
[36] R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, Germany, 2000.
72